
Apartment holiday rentals in Wintergreen Resort
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Top-rated apartment rentals in Wintergreen Resort
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Tips Up: Cozy Slopeside Retreat w/ Fireplace
The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

Panoramic Sunsets, Mountain Views, Private Deck.
Wake up above the mountains and end your day with unforgettable sunset views some of the best on the mountain. Sunset Vista Villa is a cozy retreat designed for slowing down, morning coffee on the deck, evenings by the fire. With two private bedrooms, each with its own en-suite bathroom, its perfect for couples or friends. Easy entry with just a few steps, yet elevated views make this stay both convenient and special. Ask us about early check-in or late check-out to enjoy even more of the view

2 bdrm/2 full bath Best Views of Blue Ridge Mtns.
Best View of the Blue Ridge Mountains! Panoramic window views from the great room, dining area and kitchen. If you want to get a closer look step out on the observation deck to see the beautiful mountains and ski slopes (seasonal). Patio furniture is on the deck to enjoy morning sunrises and evening sunsets. All new stainless steel appliances in kitchen, Freshly painted throughout. 2 bedroom 2 bath Lots of activities to do at the Wintergreen Resort all year long. Year round resort activities.

Five Minute Walk to Everything!
**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

Luxury Condo in the Sky! Finest in Wintergreen!
Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

The Modern Mountain Condo
Conveniently located within the 4-season Wintergreen Resort, this recently renovated condo offers a quiet and cozy stay while you take in the mountain views and enjoy endless outdoor activities, wineries, breweries, restaurants, and antique shops. Rest and recharge while you enjoy the light-filled, open floor plan with a wood-burning fireplace, a kitchen with plenty of cabinet space, and full-sized appliances for cooking. Private patio and community pool access are located outside the unit.

Eight Minute Walk to Everything
This one-bedroom, one-bath condo is centrally located. Ski check-in, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within an 8 minute walk. It's a one-story, downstairs unit that includes a back porch with just a few steps down to the ground. Perfect for taking the dog outside in the pet-friendly space. Full kitchen and dishes, wood-burning fireplace, balcony, and all towels and linens are provided for your convenience. Sleeps 3.

3 BR 3 BA, 2 story condo in Highlands
Newly renovated condo! You can't beat the view from up here. Top floor/vaulted ceilings, next to the Highlands Lift. Just steps from the expert slopes and on the Wintergreen shuttle route. Enjoy hiking, skiing, snowboarding, tubing, outdoor pool time or a local brewery. This condo has 2 master's with king beds, 1 bunk bed (twin over full), a single twin bed and a pull out twin sleeper sofa. The king beds have new high quality mattresses and luxury bedding and a 60" HDTV in living room

1 bedroom condo, close to hikes & breweries
Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

BlueRidge Getaway- Dog Friendly
Relax and enjoy spectacular top-floor mountain views from the deck. This recently renovated unit is at the top of the mountain close to many hiking trails. Visit the Wintergreen village, with its restaurants and shops, with a 5 minute drive or an easy hike through the woods. You also have access to Rhodes Farm and Chestnut Hills pool. This condo is convenient to Devils Backbone, Bold Rock, and the litany of other breweries, cideries, distilleries, and restaurants. Dogs welcome!

Cozy Comfort with a View - Wintergreen Resort
Our private, spacious, dog friendly condo is just a 5 minute walk to the main lodge with shops, restaurants, and of course the slopes! Shuttles run during ski season as well. Beautiful hiking trails are just outside the door, and a short drive will get you to the Blue Ridge Parkway, Crabtree Falls, Stoney Creek Golf Course, and the famous Route 151 with Virginia's finest breweries and wineries. There is a community pool available in Wintergreen Resort during the summer months.

Cozy Laurelwood condo - 10 min walk to slopes
This beautiful 1-bedroom, 1-bath Laurelwood condo is perfectly located just a short walk from the pool, market, coffee shop, restaurants, and the Wintergreen Conference Center. Inside, you’ll find a fully equipped kitchen, a cozy wood-burning fireplace (with complimentary firewood), and a spacious king-size bed. Step outside to your private deck and enjoy the peace of the surrounding forest—an ideal retreat for relaxation and comfort.
Popular amenities for Wintergreen Resort apartment rentals
Weekly apartment rentals

Wintergreen Ski Retreat, Cozy Condo Near Slopes

Wintergreen! Dog friendly, cozy and comfortable

Spacious Ski In Ski Out Condo with Mountain View

Recently updated - views of the Blue Ridge Mtns

Ski- In/Ski-Out Comfy Condo

Beautiful Views/WalktoResort&Hiking/PupFriendly

Love of mountains oh fill my cup

Happy hour on the 18th Hole
Pet-friendly apartment rentals

All-Season 2bd/2ba next to Spa view of Golf Course

On the mountain, pet and child friendly

Ski-In Ski-Out ~ Mtn Views ~ King Suite

Mountain Views

Condo with Valley Views!

Buena Vista Panoramic Retreat: Million Dollar View

New Construction! 1 Bed/2 Bath, pet friendly

Nature’s Haven 1 Bedroom Condo Wintergreen Resort
Apartment rentals with a pool

Pepper's Mountain Pad

Uncork and unwind Mountain Retreat

2 br/2 b condo; skiing; hiking; wineries; pool

Mountain Inn Lodge 63 with Wintergreen Advantage

Amazing views! Overlooking Expert Slope

A Mountain Escape-Cozy Condo for 2 to 4

Great Views & Great Reviews + Pizza

Birds Eye: Mntn Views K-Bed DogOK Pool Tennis Golf
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £119 | £119 | £104 | £97 | £94 | £94 | £103 | £98 | £97 | £111 | £106 | £124 |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about apartment rentals in Wintergreen Resort

Total holiday rentals
Explore 320 holiday rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort holiday rentals start at £60 per night before taxes and fees

Verified guest reviews
Over 9,750 verified reviews to help you choose

Family-friendly holiday rentals
190 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
250 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
320 of Wintergreen Resort holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wintergreen Resort rentals

4.9 Average rating
Wintergreen Resort stays are highly rated by guests – averaging 4.9 out of 5!
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- Shenandoah National Park
- Early Mountain Winery
- University of Virginia
- Downtown Mall
- James Monroe's Highland
- Wintergreen Resort
- Blenheim Vineyards
- Frontier Culture Museum
- Cardinal Point Winery
- Homestead Ski Slopes
- Devils Backbone Brewing Co Basecamp
- Amazement Square
- John Paul Jones Arena
- Liberty Mountain Snowflex Centre
- Monticello
- Glass House Winery
- James Madison University
- Virginia Horse Center
- The Rotunda
- Grand Caverns
- White Lotus Eco Spa Retreat
- James Madison's Montpelier
- Natural Bridge State Park
- IX Art Park




